Sodium ethanethiolate → Benzenesulfonamide

HRID 1063975Notes

Reaction equation

HRID 1063975 reaction equation
C[C@@:2]1([S:13]([NH2:16])(=[O:15])=[O:14])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]1CCCCBr.[S-]CC.[Na+]>O1CCCC1>[C:2]1([S:13]([NH2:16])(=[O:15])=[O:14])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4459711Sodium ethanethiolateHCID 131725218HCID 131725218, compound

Product 1

HCID 7370BenzenesulfonamideYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of 4-chloro-N-[5-chloro-2-(acetoxymethyl)phenyl]-N-[(R)-1-methyl-4-bromobutyl-benzenesulfonamide (0.650 g, 1.24 mmol) in tetrahydrofuran (2 mL) was added sodium thioethoxide (0.115 g, 1.36 mmol) under nitrogen at 0° C. The mixture was stirred overnight at 22° C. The mixture was quenched with 2M NaOH (3 mL), extracted with ethyl ether (2×20 mL), dried over Na2SO4, and filtered. The organic solvent was concentrated under reduced pressure. Silica gel chromatography (1:9 ethyl acetate:hexanes) afforded 0.500 g of 4-chloro-N-[5-chloro-2-(hydroxymethyl)phenyl]-N-[4-(ethylthio)]-1-(R)-methylbutyl]benzenesulfonamide as a yellow oil in 87% yield. MS (ESI+), 462 (M+H)+.

Workup

  1. customThe mixture was quenched with 2M NaOH (3 mL)
  2. extractionextracted with ethyl ether (2×20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe organic solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-972747e85f894707a3a950a636a02515
Source dataset
uspto-grants-2005_11
Patent number
US06967196B1

Reaction notes

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